


Only Awkward if You Let it Be Awkward

by Boxstorm



Category: Check Please! (Webcomic)
Genre: Awkward Sex, First Time, M/M, like so awkward
Language: English
Status: Completed
Published: 2017-04-28
Updated: 2017-04-28
Packaged: 2018-10-25 03:34:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,247
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10755876
Author URL: https://archiveofourown.org/users/Boxstorm/pseuds/Boxstorm
Summary: In which Ransom and Holster have the most awkward first time possible, and things somehow work out okay anyway





	Only Awkward if You Let it Be Awkward

It starts with Justin and March breaking up over winter break senior year. Justin tells Adam, repeatedly and emphatically, that it was a mutual decision based on a desire for more free time and a mutual fizzling of attraction. Justin says they’re still friends, and they move on quickly and quietly.

 

It starts with Justin casually mentioning a desire to explore his sexuality while he’s still in college. 

 

He’d come to Samwell for a reason, after all, and he’d like to know, going into the real world, if he’s actually as straight as he’s always assumed. 

 

It starts with Adam casually ( _ painfully  _ casually) offering his services in that department. Hoping that maybe, just maybe, he’ll convince Justin that he’s a viable option now that March is out of the picture. 

 

It somehow surprises Justin, and Adam is torn between relief that he’s been hiding whatever he feels for Justin so well, and frustration that Justin doesn’t know him as well as he thought.

 

Either way, he manages to shrug, and make some off-hand (and  _ casual _ ) remark about being bi, and having had an experience or two (or seven) while playing in Waterloo.

 

Justin shrugs just as casually and says he’ll think about it, and that’s the end of it for a while.

 

Justin goes back to his studying, and Adam goes back to his pining, and the status quo is restored.

 

Until the weekend.

  
  


“Hey,” Justin says, hovering by the door to the attic, “So you’re…?”

 

Adam blinks at him. He has a feeling he knows where this conversation is going, but he kind of hopes he’s wrong. When Justin hadn’t brought it up, Adam had hoped that maybe Justin had chosen to ignore Adam’s awkward offer, but the way Justin is looking anywhere but at Adam, and trying to wring his hands as subtly as possible makes his intentions pretty clear. 

 

“Tall?” Adam supplies helpfully, “Blond? Devastatingly handsome?”

 

“Uh, the-” Justin coughs awkwardly, “That last one?”

 

“Oh,” Adam says, feeling a warm flush race across his cheeks, just as Justin starts immediately backtracking.

 

“I mean- shit, nevermind, you probably weren’t even-” Justin babbles, stumbling backwards towards the attic door.

 

“Hey, no!” Adam says, equally awkward, “I wouldn’t have offered if I didn’t- I just thought  _ you  _ wouldn’t-”

 

“Why would  _ I _ not-,” Justin asks, freezing where he stands, eyes wide, “Look at you!” 

 

“Look at  _ me _ ?” Adam asks, because okay, he has that whole previously mentioned tall, blond thing going for him, and his abs have, on one fairly notable occasion been described as “spectacular”, but Justin is  _ Justin _ . He’s been in The Swallow’s 50- most beautiful three times; he’s built like something out of a men's magazine,  _ after  _ photoshop; basically he’s fucking flawless and Adam can’t believe Justin would be talking about  _ him  _ like that. 

 

“Look at  _ you _ ,” Adam continues, “Dude, you’re fucking perfect. If you want to, like… experiment with someone, you can get whoever you want. It doesn’t have to be me. I just figured I’d offer, like, on the off chance?”

 

“Nah, bro,” Justin says, “I want it to be you.”

 

“Chill,” Adam says, immediately cringing internally because how fucking smooth can he get, honestly. 

 

“Cool, so…,” Justin says, returning to his awkward hovering; taking a half-step forward before hopping back again.

 

Adam stands from the bed, taking an equally abortive step towards Justin. 

 

“Can I kiss you?” Adam blurts, “I mean- would that be weird?”

 

“Is any of this not weird, bro?” Justin asks.

 

“Is that a yes?” Adam asks, instead of analyzing the stab of… something that hits his chest as he remembers that Justin isn’t even half as into this as he is; at least not in the same way. 

 

Justin shrugs, and takes a more definitive step forward. 

 

It isn’t the enthusiastic confirmation Adam was hoping for, but Justin settles a hand on his shoulder and one on the side of his neck, when he meets him in the middle of the room, and he doesn’t pull back when Adam leans in to carefully press their mouths together. 

 

Justin makes a surprised sort of ‘ _ oh _ ’ sound, and his fingers tighten on Adam’s shoulder and Adam is just encouraged enough by this to deepen the kiss, and move his hands from where they’re carefully fisted on his own thighs to the back of Justin’s neck, and Justin’s lower back. 

 

Justin sighs into the kiss, moving his hand into Adam’s hair and using it to pull Adam even closer. Adam goes willingly, cautiously letting his hand slide down over the swell of Justin’s ass.

 

Justin gasps and pulls back, eyes closed.

 

“Shit, sorry,” Adam says, immediately retracting both of his hands and putting them behind himself to prevent further issues.

 

“No,” Justin manages after a second, “It was good. I just didn’t expect…”

 

“Oh,” Adam says, “Should I…?”

 

Justin grins and grabs Adam’s forearms, pulling his hands back towards himself and placing them both firmly on Justin’s ass. 

 

“Yeah,” Justin says.

 

Adam takes that as his cue to surge forward and kiss Justin stupid again. Justin’s hands both find their way into his hair, and by the time they pull apart again, they’re both gasping for breath.

 

“So?” Adam asks.

 

“I always wondered how you pulled so hard when you’re so bad at wheeling chicks,” Justin says, a little out of breath.

 

“And?” Adam asks, because that could still go either way as far as he’s concerned.

 

“And now I know,” Justin says, “If you fuck half as good as you kiss it all makes perfect sense.”

 

“You’re welcome to find out,” Adam quips without thinking.

 

“...Okay,” Justin says hesitantly.

 

“Dude, you  _ really _ don’t have to,” Adam stresses, “If you’re not one hundred percent into it, I’m not going to do it.”

 

“I mean,” Justin starts, “Like, what are we talking about… specifically.”

 

“Whatever you want,” Adam answers immediately, “Whatever you’re comfortable with or want to try or whatever. I’m here for it.”

 

“Anything?” Justin asks, “So, like, if I asked you to rim me?” 

 

“Do you want me to rim you?” Adam asks, carefully raising an eyebrow. He would. Absolutely. No questions asked. But he feels like that’s kind of a big first step. 

 

“No.” Justin says.

 

“Then no, dude,” Adam says, “Look, do you want me to just suggest things and you can say yes or no?”

 

“Yes,” Justin says, too quickly for it to be anything but a massive relief.

 

“Cool, okay,” Adam says, “So, like, handjobs and blowjobs are pretty standard across the board. Like, my hands are probably bigger than anyone you’ve been with, but it’s not going to feel massively different. That said it could be a good starting point to get you, you know…  _ into  _ it.”

 

“Oh, uh…” Justin says, shifting awkwardly from foot to foot, “Not actually a concern.”

 

“You- oh,” Adam says, “Really? Like… You’re-”

 

“You’re a  _ really _ good kisser,” Justin insists.

 

“Okay, well, uh… Great,” Adam says, smiling, pleased despite himself, “So okay, if you want to start easy we can go with that, or like. Mutual masturbation?”

 

“That-” Justin starts, voice cracking halfway through, “That sounds good.”

 

“We should move to the bed,” Adam suggests, “I know some guys can do this kind of thing standing up, but my knees tend to give up halfway through.”

 

“Yeah,” Justin says, allowing himself to be towed over to the bed and gently settling himself on the bottom bunk. 

 

“So,” Adam says, settling down next to Justin after a brief pause, “This next part tends to work better without pants. Just a thought.”

 

“Oh, right,” Justin says, standing up again to slowly undo the button on his jeans.

 

Adam wiggles out of his own pants without getting up, just lifting his hips to pull them down and off when it comes to that. 

 

He’s got a great view of Justin’s ass from where he’s sitting and as much as he kind of feels like a perv for looking (old habits die hard), he also doesn’t want to pass up this opportunity. Justin’s ass is phenomenal. 

 

Justin turns around once he has his pants off, eyes flicking down to Adam’s obviously-tented boxer-briefs and then back up, as though he’s feeling just as awkward about looking as Adam is. 

He’s hovering again, and Adam reaches out for him, pulling him in between his knees with his hands on Justin’s hips.

 

“You seem nervous,” Adam says, quietly, “We don’t have to do this.”

 

Justin crowds up against him, his chest right up in front of Adam’s face and his hands on Adam’s shoulders, and Adam can’t help but press a quick kiss to the underside of one of Justin’s pecs. He feels his stubble scrape against Justin’s skin, and he feels Justin shiver under his hands, and he pulls his face back enough to look at Justin’s face and take in his expression.

 

“I’m good,” Justin breathes, sinking further against Adam.

 

Adam slips a hand behind each of Justin’s thighs and tugs gently until Justin is straddling his lap on the bed and leaning down to kiss him again. 

 

“Are you sure?” Adam asks, “Because we could also just make out.”

 

“I’m  _ good _ ,” Justin repeats, grinding his hips down.

 

“Fuck, okay,” Adam says, “Do that again.”

 

Justin does, as Adam lifts his hips up to meet him and it’s  _ good _ , it’s  _ so fucking good _ . Adam pulls Justin down to him with a hand on the back of his neck, digging the fingers of his other hand into Justin’s thigh, and slipping his tongue into Justin’s mouth. 

 

Justin slowly goes pliant against him, sighing occasionally as Adam’s hands work their way over Justin’s body, smoothing along soft skin and digging into muscle. 

 

When he feels like Justin is relaxed enough, Adam slowly tips him sideways, laying him out next to Adam on the bed. 

 

Justin blinks his eyes open, almost sleepily, smiling up at Adam and trailing a hand across his jaw and down his neck.

 

“You good?” Adam asks, one more time, just to be sure.

 

“Yeah,” Justin says, “Yeah, I’m good.”

 

Adam grins and quickly kisses him again. 

 

Just because he can.

 

Just because he might not be able to after this. 

 

“Do you want me to start?” Adam asks, reaching out slowly to lay a large, warm hand over Justin’s dick, feeling the heat seeping through the fabric of his boxers, and the dampness collecting around the head.

 

“Yeah,” Justin breathes, hips jerking further into Adam’s hand, “Please-”

 

Adam squeezes, and Justin gasps out a gratifying, “Fuck Holtzy, please!” 

 

Adam slips a hand into Justin’s boxers to get skin on skin, shifting on the bed to get a better angle as he starts to stroke Justin’s cock in earnest. 

 

“Shit,” Justin hisses, hands clenching in the sheets beside him, eyes squeezed shut and hips thrusting up in abortive little jerks, seeking more friction from Adam’s hand. 

 

“We could just do this,” Adam says, mouthing at Justin’s ear, “You don’t have to do anything.”

 

“No,” Justin insists firmly, opening his eyes and reaching out to run a hand down Adam’s back, “I want to. Let me…?”

 

Adam pulls back, sits up on his knees, hand still moving slowly and gently on Justin’s dick. He uses his other hand to pull his own dick out of his underwear, giving it a gentle tug and watching how Justin’s eyes follow his hand. 

 

Justin shifts to sit up as well, and reaches out tentatively to wrap his hand gently around Adam’s cock.

 

And then he just kind of holds it.

 

For what Adam feels is a genuinely unreasonable amount of time. 

 

“What are you doing?” Adam finally asks, patient as a saint, as far as he’s concerned.

 

“This is the first time I’ve done this,” Justin defends himself. 

 

“It’s not like you’ve never had your hand on a dick before,” Adam points out.

 

“Yeah, but it’s always been  _ my  _ dick,” Justin says.

 

“The basic principle is the same,” Adam says, “Just do what you normally do. But like… a foot to the left.”

 

“It’s just weird,” Justin says, giving an experimental squeeze and sliding his hand slowly up from base to tip. 

 

“Fuck, yeah, like that,” Adam gasps.

 

“Oh,” Justin says, “Yeah?”

 

“Yeah, bro,” Adam says, trying to keep his hips still so he doesn’t scare Justin off, “Just keep doing that.”

 

Justin has always been a quick study; it’s how he somehow has a 4.0 without ever going to class, and this is no different. He spends maybe a minute figuring out what Adam does and doesn’t like, and then he just fucking  _ ruins _ Adam from one heartbeat to the next, squeezing tight and tugging hard and biting down on Adam’s shoulder in a way that will definitely leave a mark. 

 

“ _ Fuck me _ ,” Adam groans, leaning his weight against Justin’s chest, unable to hold himself up any longer. 

 

“Can I?” Justin asks, slowing his hand, loosening his grip, panting against Adam’s neck.

 

“Do you want to?” Adam asks, “Really?”

 

He feels Justin nod against his shoulder.

 

“Fuck yeah, dude,” Adam says, “Whatever you want. I mean that.”

 

“I want to fuck you,” Justin says firmly, sitting up to look Adam in the eye.

 

Adam groans wordlessly, catches Justin’s lips in a searing kiss, then unfolds himself to drop to the floor and wiggle half under the bed.

 

“Where are you going?” Justin asks, peeking over the edge of the bed, even though Adam knows that all that’s visible is his ass and legs.

 

“Lube,” Adam says, voice muffled, grabbing the bottle from where he’d stashed it and wiggling just as gracelessly back out. He takes a second to strip his underwear off, before settling back on the bed. 

 

“Oh, right,” Justin says, “So should I…?”

 

“Oh, uh, no…,” Adam says, “I’ll do it myself, I think, this time. Just to be safe.”

 

Fuck.  _ This time _ . What is he saying? Like there’s going to be a  _ next time _ . Like Justin would ever want to do this again, as more than just a means to satisfy his curiosity. 

 

Adam quickly slicks up a finger and runs it between his ass cheeks, and his mind gratifyingly blanks out for one blissful moment. 

 

When his brain comes back online, it’s to the sound of a deep groan from Justin.

 

“Can you turn?” Justin asks.

 

Adam blinks at him in confusion, even as he’s gently running his finger back and forth over his hole.

 

“I want to see,” Justin says, voice catching as Adam finally sinks the tip of his finger in and lets out a quiet whine. 

 

Adam huffs out a breath and pulls his finger back out, carefully turning around. He pops up slightly on his knees, and drops his face down onto the mattress, getting back down to business. 

 

He can hear the unmistakable sounds of Justin’s hand stroking up and down his cock as Adam slips his finger carefully in and out, and it edges him into adding a second finger.

 

He hears Justin’s sharp intake of breath as he works himself open; hears Justin’s hand speed up.

 

“Don’t come yet,” Adam says, turning his head, and  _ wow _ , that’s an image he doesn’t want to let go of any time soon; Justin on his knees, head tipped back but eyes on Adam’s ass, one hand running up and down his chest and the other gripping his dick tightly, precum beading at the head. 

 

“Don’t worry,” Justin says, lifting his head to grin at Adam, “I’m still going to fuck you.”

 

“You fucking better,” Adam manages to choke out, even as he adds a third finger. 

 

“Fuck,” Justin says, “Fuck, holy shit.”

 

“Fuck,” Adam agrees, “Condom?”

 

“Shit, yeah, hang on,” Justin says, “Wait there. Don’t move.”

 

Justin unfolds and half-throws himself off the bed and towards the dresser across the room.

 

“Or, like… Keep moving. If you need to. I don’t know how this works,” Justin continues, digging around in the detritus on top of the dresser until he finally comes away, triumphant, with a condom clutched in one hand.

 

“I’m good,” Adam says, still gently moving his fingers, “I’m ready. Get over here.”

 

Justin fucking somehow glides back to the bed, unfairly graceful even rock hard and leaking with eyes half-lidded and what looks like a smear of lube over one nipple. He slides a hand gently across Adam’s back as he settles onto the bed, and Adam can’t suppress the shiver that follows. 

 

Adam hands back the bottle of lube with his unoccupied hand, drops his head back down onto the mattress and focuses on breathing as he hears Justin tear open the condom packet, and hiss gently as he presumably rolls it into place. 

 

Adam hears the click of the lube opening, the squelch of Justin slicking up his dick, and then his brain gives up again as he feels the blunt pressure of Justin’s cock against his ass. 

 

“You good?” Justin asks, not pressing in, just resting the head of his cock against Adam’s hole.

 

“Yeah,” Adam breathes, “Please.”

 

His voice cracks in the middle as Justin finally, painfully slowly, pushes his way in. 

 

They both groan in tandem, as in sync in this as in everything, apparently, and it isn’t long until Justin is fully sheathed inside Adam, panting hard and shuddering. 

 

“How are you doing?” Justin asks after a moment, sounding bizarrely formal for someone with his dick in his best bro’s ass.

 

“Yeah,” Adam says, before realizing that that isn’t really an answer, “I’m good. Just… stay still for a sec.”

 

Justin keeps his hips steady, but runs a hand soothingly over Adam’s hip.

 

“Whenever you’re ready, bro,” Justin says, not to pressure Adam, he’s sure, but to give Adam control over how this goes.

 

He’s so fucking thoughtful like that, and Adam has to take a moment to get his emotions in check more than to adjust to Justin’s not-insubstantial girth. 

 

“Okay,” Adam says when his eyes and ass have both stopped burning. 

 

“Okay?” Justin asks, holding still for a beat longer, hand shifting to the small of Adam’s back. 

 

“Yeah,” Adam breathes, even though he can feel Justin’s hand on him like a brand, hot and dry and burning into his skin.

 

“Start slow,” he instructs, voice muffled into a pillow that he’s grabbed to rest his head on.

 

“‘Course, bro,” Justin says.

 

And then he’s pulling out, slow and smooth and  _ perfect _ .

 

Adam isn’t sure what sounds he’s making, paying more attention to the little grunts and groans coming from behind him as Justin stops just before he pulls all the way out to slide back in equally slowly. 

 

He keeps up this pace, slow even thrusts of his hips, not speeding up even minutely, although it must be difficult to hold back, until finally Adam lifts his head slightly to give himself a bit more leverage and snaps his hips back as hard as he can.

 

Justin shouts, a wordless sound of surprise and pleasure, and his hands fly to Adam’s hips, fingers digging into the muscle hard enough to bruise. “Fuck,” Justin says when he catches his breath, “Warn a guy.”

 

“Fuck me,” Adam says instead of replying, “Just- fuck me harder. Please.”

 

“Yeah,” Justin breathes, and he does as he’s told, holding Adam’s hips firm as he picks up the pace, starting up a steady rhythm of skin-on-skin.

 

Adam lets his head drop back down, letting the pillow muffle the embarrassing whines that Justin is pushing out of him.

 

“Fuck,” Justin says again, “Fuck, fuck, bro, holy shit.”

 

Each word sounds punched out of him, like he’s trying to hold them in but can’t. 

 

“So fucking good, bro,” Justin continues, “Can’t believe we could’ve been doing this…”

 

He trails off, picking up the pace, but Adam’s brain has snagged on that tiny phrase and won’t let it go.

 

‘ _ We could’ve been doing this… _ ’

 

Like maybe Justin has thought about doing this?

 

But no, that’s not right. Justin had March until a few weeks ago. Justin was firmly straight until a few days ago. Justin hadn’t thought about having sex with  _ any _ man, let alone with Adam until a few hours ago. 

 

Adam is  _ projecting like a champ _ , and he needs to  _ stop _ before he gets hurt.

 

More hurt.

 

Whatever.

 

He tries to focus on the feeling of Justin’s cock pumping into his ass, the feeling of Justin’s thighs slapping into his own, the feeling of Justin’s hand gently stroking across Adam’s abs. 

 

He’s distracted by a prickling behind his eyes instead.

 

And that’s when Adam lets out a chest-rattling sob. 

 

“Are you- fuck, are you  _ crying _ ?” Justin asks, hips stopping dead, dick halfway into Adam’s ass.

 

“It’s fine,” Adam cuts in, wiping harshly at his eyes, “keep going.”

 

“Dude,  _ no _ ,” Justin says, “What the fuck. Am I hurting you? Jesus!”

 

“I’m fine,” Adam insists, because fuck everything, he  _ should be fine _ .

 

“No,” Justin says, “I’m stopping. Let me just-”

 

Adam honest-to-God  _ whimpers _ as Justin pulls out, and he’s such a fucking  _ mess _ . Why couldn’t he just keep it together for five more minutes and  _ not _ completely ruin Justin’s first time with a dude. 

 

Justin carefully lays himself down next to Adam, draping an arm across Adam’s chest, and it’s all too fucking much, and the God damn tears start up again and he can’t fucking stop them.

 

“Bro,” Justin says, voice quiet and careful, “Do I have to, like, take you to the hospital or something?”

 

Adam chokes out a laugh between sobs, because of course Justin is worried he’d hurt him. Justin is fucking perfect and Adam is fucking  _ crying _ and can’t even explain  _ why _ .

 

“No, dude, I’m fine,” Adam tries again, turning around in Justin’s arms to face him. 

 

“You seem, like, the opposite of fine,” Justin points out. 

 

And the thing is, Adam has never been able to lie well, and especially not when he’s this emotional, and  _ especially  _ not to Justin. 

 

“Okay,” Adam admits, “I’m not… great. But I want you to keep going. Because this is about you, not me.”

 

“Bullshit,” Justin says, “Consent is a two-way deal, man. I’m not going to keep going when you obviously don’t want me to.”

 

“I do!” Adam insists, “I want you to keep going. I just…”

 

“What?” Justin asks.

 

“I just… fuck, I want  _ more  _ than that,” Adam says, “And it’s so fucking selfish and I  _ know  _ that, but I can’t help it, Rans. I’ve fucking tried and I can’t fix it and  _ now _ I’ve fucked everything up because I had to go and offer to fuck you even though I knew it was a bad idea, and  _ then _ , I couldn’t even do that right.”

 

“Wow,” Justin says.

 

“Yeah,” Adam agrees, because even though he never meant to say that much, and even though he’s definitely fucked this relationship beyond repair, it feels just a little bit good to get it all out in the open.

 

“So…” Justin says, “You like me… and that’s why you’re crying.”

 

“Yeah, pretty much,” Adam sighs, “I can, like… I dunno, leave or something? If you want?”

 

“Dude, of course not,” Justin says, “This is perfect.”

 

“What?” Adam asks, because  _ what _ ?

 

“I mean, not the crying, obviously,” Justin continues, “But like, the rest of it. That’s fucking sw’awesome, bro.”

 

“I don’t-” Adam says, firmly at a loss.

 

When he’d allowed himself to consider telling Justin, he had, without fail, imagined Justin being somewhere between uncomfortable and furious. This is clearly neither of those things, and Adam doesn’t really know what to do with that.

 

“Dude, I would be so fucking down for more than just fucking,” Justin says, propping himself up on one elbow to catch Adam’s eyes. 

 

“What?” Adam asks, voice still embarrassingly watery.

 

“I’m fucking gone on you, bro,” Justin says, stroking a hand gently over Adam’s abs. 

 

“I don’t-” Adam says again, stuck in some sort of feedback loop while his brain simultaneously tells him that Justin is giving him everything he wants, and that it’s far too good to be true.

 

“I don’t really know how to be clearer here,” Justin admits, “Like, I love you, bro. And I think we should keep fucking, definitely, because I’m, like, hella into this? But we should also, like, date and shit? If that’s even what you meant. Shit, is that what you meant?”

 

“That’s exactly what I meant,” Adam chokes out quickly, stopping Justin’s spiral in its tracks, and grabbing his hand where he’s pulling it away. 

 

“Oh, okay,” Justin says, “Sw’awesome.”

 

“Sw’awesome,” Adam repeats, “So do you want to…”

 

He trails off, gesturing vaguely between their dicks.

 

Adam’s has softened fully, likely from the crying and the existential crisis, but Justin is still half-hard, and Adam feels like he should be doing something about that. 

 

“Nah,” Justin says, “Plenty of time for that later. You look like you need some bro-cuddling instead.”

 

Justin snuggles into him, tangling their legs together like it’s that easy. Like he gets to just  _ have  _ this. No questions, no arguments, just Justin, handed to him without issue. 

 

It’s heady, and more than a little bit overwhelming. 

 

“Bro,” Justin says, mouth pressed into Adam’s shoulder and muffling his words, “You don’t have to think this hard. Just let me  _ love you _ .”

 

Justin raises his voice on the last two words, injecting a dramatic, sing-song quality that Adam knows Justin knows is guaranteed to make Adam laugh. 

 

Justin wiggles even closer and, honestly it’s a lot less comfortable than it was a minute ago, but fuck it.

 

It’s still perfect. 

 

**Author's Note:**

> If this is the kind of thing you enjoy, I can also be followed on tumblr at boxstorm.tumblr.com :D


End file.
